EP2624818B1 - Mit borsäure stabilisierte bortezomib-formulierungen - Google Patents
Mit borsäure stabilisierte bortezomib-formulierungen Download PDFInfo
- Publication number
- EP2624818B1 EP2624818B1 EP11770615.0A EP11770615A EP2624818B1 EP 2624818 B1 EP2624818 B1 EP 2624818B1 EP 11770615 A EP11770615 A EP 11770615A EP 2624818 B1 EP2624818 B1 EP 2624818B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bortezomib
- boric acid
- glycine
- composition
- mass ratio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Not-in-force
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/22—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
Definitions
- a lyophilized powder formed from 3.5 mg bortezomib dissolved in 5 mL t -butyl alcohol is reported as having impurity levels below 0.5% (relative to the bortezomib content) after storage for 1 week at 60°C in a closed container, at 40°C and 75% relative humidity, or at 25°C and 60% relative humidity.
- WO 2009/154737 A1 discloses lyophilised bortezomib compositions containing glycine as bulking agent.
- a method of making a solid composition that includes forming a liquid mixture including a solvent, bortezomib and boric acid, wherein the mass ratio of boric acid to bortezomib is from 2:1 to 10:1, and wherein the liquid mixture further comprises glycine, where the mass ratio of glycine to bortezomib is from 1:1 to 20:1, and lyophilizing the liquid mixture.
- the solid composition included bortezomib, boric acid and glycine, with at most trace amounts of water and/or ethanol.
- Cool water for injection (9 Liters, USP, 15°-30°C) was added to a clean compounding vessel covered with aluminum foil to protect the interior from light and then sparged with nitrogen until the dissolved oxygen level was below 2 parts per million (ppm).
- Boric acid 51 grams was added to the water and mixed at room temperature (15°-30°C) until dissolved.
- Glycine 150 grams was then added, and the liquid was mixed at room temperature until the glycine was dissolved. Approximately 1,500 mL of this solution was removed and reserved for use as a rinse solution.
- Sparged water for injection was added to the compounding vessel to obtain a final volume of 12 liters, and the liquid was mixed for approximately 10 minutes. The mixture was pre-filtered through a 0.45 micron filter and subsequently through a 0.22 micron filter. Aliquots (2 mL) of the filtered solution were added to vials that were then partially stoppered.
- the bortezomib compositions containing glycine and boric acid had substantially reduced reconstitution times relative to bortezomib compositions containing glycine alone.
- a reduction in reconstitution time when boric acid was present also was observed for bortezomib compositions containing dextran or hydroxypropyl- ⁇ -cyclodextrin.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Claims (14)
- Zusammensetzung, umfassend:Bortezomib undBorsäure;wobei die Zusammensetzung ein Feststoff ist, unddas Massenverhältnis von Borsäure zu Bortezomib 2:1 bis 10:1 beträgt, wobei die Zusammensetzung ferner Glycin umfasst, wobei das Massenverhältnis von Glycin zu Bortezomib 1:1 bis 20:1 beträgt.
- Zusammensetzung nach Anspruch 1, wobei das Massenverhältnis von Borsäure zu Bortezomib 2:1 bis 4:1 oder 2:1 bis 3:1 beträgt.
- Zusammensetzung nach Anspruch 1 oder Anspruch 2, wobei das Massenverhältnis von Glycin zu Bortezomib 5:1 bis 15:1 oder 7:1 bis 10:1 beträgt.
- Zusammensetzung nach Anspruch 3, wobei das Massenverhältnis von Borsäure zu Bortezomib etwa 3:1 beträgt und das Massenverhältnis von Glycin zu Bortezomib etwa 7:1 beträgt.
- Zusammensetzung nach Anspruch 4, die etwa 3,5 mg Bortezomib, etwa 10,5 mg Borsäure und etwa 25 mg Glycin umfasst.
- Zusammensetzung nach Anspruch 1 oder Anspruch 2, ferner umfassend Mannit, wobei das Massenverhältnis von Mannit zu Bortezomib 1:1 bis 20:1 beträgt.
- Zusammensetzung nach einem der vorhergehenden Ansprüche, wobei mindestens ein Teil des Bortezomibs in der Zusammensetzung in einer Anhydridstruktur vorliegt oder mindestens ein Teil des Bortezomibs und der Borsäure zusammen in der Zusammensetzung in einer Anhydridstruktur vorliegen.
- Zusammensetzung nach einem der vorhergehenden Ansprüche, wobei, wenn die Zusammensetzung bei 55 °C gelagert wird, nach 3 Wochen höchstens 5 % des Bortezomibs zerfallen, nach 3 Wochen höchstens 2 % des Bortezomibs zerfallen, nach 3 Wochen höchstens 1 % des Bortezomibs zerfällt oder nach 3 Wochen höchstens 0,5 % des Bortezomibs zerfällt.
- Zusammensetzung nach einem der vorhergehenden Ansprüche, wobei die Zusammensetzung innerhalb von 4 Minuten, innerhalb von 3 Minuten, innerhalb von 1 Minute oder innerhalb von 30 Sekunden eine Lösung oder eine Emulsion bildet, wenn die Zusammensetzung in einer Bortezomib-Konzentration von 1 mg/ml Salzlösung mit einer 0,9 % NaCl-Salzlösung kombiniert und alle 15 Sekunden manuell geschüttelt wird.
- Verfahren zum Herstellen einer festen Zusammensetzung, umfassend:Bilden einer flüssigen Mischung, die ein Lösungsmittel, Bortezomib und Borsäure umfasst, wobei das Massenverhältnis von Borsäure zu Bortezomib 2:1 bis 10:1 beträgt, und wobei die flüssige Mischung ferner Glycin umfasst, wobei das Massenverhältnis von Glycin zu Bortezomib 1:1 bis 20:1 beträgt; undLyophilisieren der flüssigen Mischung.
- Verfahren nach Anspruch 10, wobei das Lösungsmittel Wasser umfasst, und wobei das Lösungsmittel ferner 1 bis 20 Vol.% eines organischen Lösungsmittels und vorzugsweise 2 bis 10 Vol.% eines organischen Lösungsmittels oder etwa 5 Vol.% Ethanol umfasst.
- Verfahren nach Anspruch 10 oder Anspruch 11, wobei das Massenverhältnis von Borsäure zu Bortezomib 2:1 bis 4:1 oder 2:1 bis 3:1 beträgt.
- Verfahren nach einem der Ansprüche 10 bis 12, wobei das Massenverhältnis von Glycin zu Bortezomib in der flüssigen Mischung 5:1 bis 15:1 oder 7:1 bis 10:1 beträgt.
- Verfahren nach Anspruch 13, wobei das Massenverhältnis von Borsäure zu Bortezomib in der flüssigen Mischung etwa 3:1 beträgt, das Massenverhältnis von Glycin zu Bortezomib in der flüssigen Mischung etwa 7:1 beträgt und das Lösungsmittel Wasser und etwa 5 Vol.% Ethanol umfasst.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39004610P | 2010-10-05 | 2010-10-05 | |
PCT/US2011/054703 WO2012047845A1 (en) | 2010-10-05 | 2011-10-04 | Bortezomib formulations stabilised with boric |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2624818A1 EP2624818A1 (de) | 2013-08-14 |
EP2624818B1 true EP2624818B1 (de) | 2017-04-05 |
Family
ID=44802402
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11770615.0A Not-in-force EP2624818B1 (de) | 2010-10-05 | 2011-10-04 | Mit borsäure stabilisierte bortezomib-formulierungen |
Country Status (5)
Country | Link |
---|---|
US (1) | US8962572B2 (de) |
EP (1) | EP2624818B1 (de) |
AU (1) | AU2011312264B2 (de) |
CA (1) | CA2813003A1 (de) |
WO (1) | WO2012047845A1 (de) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2013227219A1 (en) | 2012-03-02 | 2014-10-23 | Dr. Reddy's Laboratories Limited | Pharmaceutical compositions comprising boronic acid compounds |
EA021179B1 (ru) * | 2012-06-15 | 2015-04-30 | Ощество С Ограниченной Ответственностью "Тева" | Лиофилизат соединения бороновой кислоты |
CN103070835B (zh) * | 2013-01-31 | 2015-01-07 | 江苏奥赛康药业股份有限公司 | 一种含硼替佐米的冻干组合物及其制备方法 |
CN103142509B (zh) * | 2013-03-06 | 2018-01-02 | 石药集团中奇制药技术(石家庄)有限公司 | 一种注射用硼替佐米药物组合物 |
CN103212055B (zh) * | 2013-04-19 | 2014-11-05 | 海南锦瑞制药股份有限公司 | 一种硼替佐米的药物组合物及其制备方法 |
CN104414982B (zh) * | 2013-08-28 | 2018-06-22 | 山东新时代药业有限公司 | 一种硼替佐米冻干粉针剂及其制备方法 |
CN104586776B (zh) * | 2013-10-30 | 2017-05-17 | 扬子江药业集团上海海尼药业有限公司 | 以硼替佐米为活性成分的制剂及其制备方法 |
US20170143622A1 (en) * | 2014-07-04 | 2017-05-25 | Dr. Reddy's Laboratories Limited | Stable liquid ready-to-use injectable formulation of bortezomib |
EP3031811A1 (de) | 2014-12-09 | 2016-06-15 | Teva Pharmaceuticals Ltd. | Apfelsäureester aus Bortezomib |
MA41505A (fr) * | 2015-02-11 | 2017-12-19 | Millennium Pharm Inc | Nouvelle forme cristalline d'un inhibiteur de protéasome |
CN105056205A (zh) * | 2015-06-29 | 2015-11-18 | 杭州华东医药集团新药研究院有限公司 | 一种含硼替佐米的药物组合物及其制备方法 |
EP3120837A1 (de) | 2015-07-22 | 2017-01-25 | Stada Arzneimittel Ag | Verfahren zur herstellung einer bortezomibester-lösung |
RU2659160C1 (ru) * | 2017-07-10 | 2018-06-28 | Акционерное Общество "Фарм-Синтез" | Способ получения лиофилизата бортезомиба и фармацевтическая композиция, содержащая бортезомиб в форме стабильного лиофилизованного продукта, полученная указанным способом |
CN109320584A (zh) * | 2017-08-01 | 2019-02-12 | 重庆医药工业研究院有限责任公司 | 一种硼替佐米的杂质及其制备方法 |
EP3836932A2 (de) | 2018-08-17 | 2021-06-23 | PTC Therapeutics, Inc. | Verfahren zur behandlung von bauchspeicheldrüsenkrebs |
EA202192117A1 (ru) * | 2019-02-28 | 2021-11-23 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способ лечения множественной миеломы |
CN110314221B (zh) * | 2019-06-29 | 2020-09-04 | 四川汇宇制药股份有限公司 | 一种注射用硼替佐米的冻干工艺 |
US11986486B2 (en) | 2020-11-02 | 2024-05-21 | Spes Pharmaceuticals Inc. | Aqueous compositions of bortezomib |
WO2023220641A2 (en) | 2022-05-11 | 2023-11-16 | Juno Therapeutics, Inc. | Methods and uses related to t cell therapy and production of same |
WO2023220655A1 (en) | 2022-05-11 | 2023-11-16 | Celgene Corporation | Methods to overcome drug resistance by re-sensitizing cancer cells to treatment with a prior therapy via treatment with a t cell therapy |
WO2024097905A1 (en) | 2022-11-02 | 2024-05-10 | Celgene Corporation | Methods of treatment with t cell therapy and immunomodulatory agent maintenance therapy |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4499082A (en) | 1983-12-05 | 1985-02-12 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid peptides |
US5187157A (en) | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
US5250720A (en) | 1987-06-05 | 1993-10-05 | The Dupont Merck Pharmaceutical Company | Intermediates for preparing peptide boronic acid inhibitors of trypsin-like proteases |
US5242904A (en) | 1987-06-05 | 1993-09-07 | The Dupont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
EP0315574A3 (de) | 1987-11-05 | 1990-08-22 | Hoechst Aktiengesellschaft | Renin-Inhibitoren |
US5106948A (en) | 1988-05-27 | 1992-04-21 | Mao Foundation For Medical Education And Research | Cytotoxic boronic acid peptide analogs |
US6083903A (en) | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
JP4162491B2 (ja) | 2001-01-25 | 2008-10-08 | アメリカ合衆国 | ボロン酸化合物製剤 |
WO2008075376A1 (en) | 2006-12-18 | 2008-06-26 | Natco Pharma Limited | Polymorphic forms of bortezomib and process for their preparation |
CN103450241A (zh) | 2008-06-17 | 2013-12-18 | 米伦纽姆医药公司 | 硼酸酯化合物及其医药组合物 |
EA201170527A1 (ru) | 2008-10-01 | 2011-10-31 | Др. Редди'С Лабораторис Лтд. | Фармацевтические композиции, включающие соединения бороновой кислоты |
EA201170921A1 (ru) | 2009-01-09 | 2012-01-30 | Сан Фарма Адвансед Ресёрч Компани Лимитед | Фармацевтическая композиция |
WO2010114770A1 (en) | 2009-03-30 | 2010-10-07 | Cerulean Pharma Inc. | Polymer-agent conjugates, particles, compositions, and related methods of use |
EP2238973A1 (de) | 2009-04-07 | 2010-10-13 | Cephalon France | Lyophilisierte Präparate von Proteasominhibitoren |
NZ602392A (en) | 2010-03-18 | 2014-03-28 | Innopharma Inc | Stable bortezomib formulations |
US8263578B2 (en) | 2010-03-18 | 2012-09-11 | Innopharma, Inc. | Stable bortezomib formulations |
-
2011
- 2011-10-04 EP EP11770615.0A patent/EP2624818B1/de not_active Not-in-force
- 2011-10-04 WO PCT/US2011/054703 patent/WO2012047845A1/en active Application Filing
- 2011-10-04 US US13/252,421 patent/US8962572B2/en active Active
- 2011-10-04 CA CA2813003A patent/CA2813003A1/en not_active Abandoned
- 2011-10-04 AU AU2011312264A patent/AU2011312264B2/en not_active Ceased
Non-Patent Citations (1)
Title |
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None * |
Also Published As
Publication number | Publication date |
---|---|
WO2012047845A1 (en) | 2012-04-12 |
US20120083457A1 (en) | 2012-04-05 |
EP2624818A1 (de) | 2013-08-14 |
US8962572B2 (en) | 2015-02-24 |
AU2011312264B2 (en) | 2015-07-02 |
CA2813003A1 (en) | 2012-04-12 |
AU2011312264A1 (en) | 2013-05-09 |
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